18471-99-3Relevant articles and documents
4-Oxoquinolines and monoamine oxidase: When tautomerism matters
Mesiti, Francesco,Maruca, Annalisa,Silva, Vera,Rocca, Roberta,Fernandes, Carlos,Remi?o, Fernando,Uriarte, Eugenio,Alcaro, Stefano,Gaspar, Alexandra,Borges, Fernanda
, (2021)
4-Oxoquinoline derivatives have been often used in drug discovery programs due to their pharmacological properties. Inspired on chromone and 4-oxoquinoline chemical structure similarity, a small series of quinoline-based compounds was obtained and screened, for the first time, toward human monoamine oxidases isoforms. The data showed the N-(3,4-dichlorophenyl)-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamide 10 was the most potent and selective MAO-B inhibitor (IC50 = 5.30 ± 0.74 nM and SI: ≥1887). The data analysis showed that prototropic tautomerism markedly influences the biological activity. The unequivocal characterisation of the quinoline tautomers was performed to understand the attained data. To our knowledge, there have been no prior reports on the characterisation of quinolone tautomers by 2D NMR techniques, namely by 1H–15N HSQC and 1H–15N HMBC, which are proposed as expedite tools for medicinal chemistry campaigns. Computational studies on enzyme-ligand complexes, obtained after MM-GBSA calculations and molecular dynamics simulations, supported the experimental data.
Palladium-Nanoparticles-Catalyzed Oxidative Annulation of Benzamides with Alkynes for the Synthesis of Isoquinolones
Sharma, Nidhi,Saha, Rajib,Parveen, Naziya,Sekar, Govindasamy
, p. 1947 - 1958 (2017/06/09)
A novel method to synthesize isoquinolones via oxidative annulation of N-alkoxy benzamides and alkynes using binaphthyl-stabilized palladium nanoparticles (Pd-BNP) as catalyst has been developed. This methodology affords various isoquinolone derivatives in good to excellent yields with high regioselectivities in the presence of air as oxidant. N-Methoxybenzothioamide was also found to undergo oxidative annulation with alkyne successfully and provided a sulfur analogue of isoquinolones in moderate yields. The Pd-BNP catalyst was easily recovered and reused up to four times without any apparent agglomeration. (Figure presented.).
Pharmacologically active amides and esters containing an azabicycloalkane moiety
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, (2008/06/13)
Compounds of formula STR1 wherein R1 is hydrogen or one or more specified substituents, X is --O-- or --NR2 -- where R2 is lower alkyl, lower alkenyl, lower alkynyl, aryl or specified substituted lower alkyl or R2/su